Synthesis of the 6- and 7-Hydroxy-5,8-dioxocarbostyrils

George Pettit, Wayne C. Fleming, Kenneth D. Paull

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Abstract

Utilizing a condensation reaction between amine I and methyl propiolate to obtain pyridone III followed by reaction with potassium t-butoxide and oxygen in dimethyl sulfoxide, a convenient synthesis of 6-hydroxy-5,8-dioxocarbostyril (V) was achieved. Conversion of 8-hydroxycarbostyril via dinitro (XII) and diamino (XIIIa) intermediates provided the isomeric 7-hydroxy-5,8-dioxocarbostyril (XV). The structures assigned to hydroxyquinones V and XV received support from mass spectral and proton magnetic resonance studies.

Original languageEnglish (US)
Pages (from-to)1089-1092
Number of pages4
JournalJournal of Organic Chemistry
Volume33
Issue number3
DOIs
StatePublished - Mar 1 1968

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ASJC Scopus subject areas

  • Organic Chemistry

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